A vineyard with rows of grapevines, a clear sky, and distant mountains.

Calzaiolo Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Calzaiolo vacation rentals

An arched entrance with a lantern above, flanked by two potted plants.

1. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (109 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is P10,149
P11,448 total
includes taxes & fees
Nov 24 - Nov 25
Villa il Fedino
A stone building with a patio area featuring a table and chairs under a large umbrella.

2. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is P5,817
P6,612 total
includes taxes & fees
Nov 29 - Nov 30
Relais Villa Olmo - Place of Charme
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

3. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (93 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is P7,372
P8,393 total
includes taxes & fees
Nov 3 - Nov 4
B&B La Fonte del Machiavelli
A tented room with a bed, curtains, and a view of an outdoor deck.

4. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.6 out of 10, Excellent, (123 reviews)
"Very helpful staff and comfortable affordable stay"
United States
Ana María
The price is P3,055
P3,574 total
includes taxes & fees
Nov 3 - Nov 4
hu Firenze Certosa camping in town
A modern house with glass walls and a patio area.

5. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (94 reviews)
"The Marignolle Relais & Charme is absolutely gorgeous. The rooms are beautifully decorated and everything is so clean. The grounds are well maintained and the pool area is stunning. We loved our two day stay and heartily recommend it. Stay here you’ll love it!!!"
Canada
Honey
The price is P8,851
P10,590 total
includes taxes & fees
Nov 29 - Nov 30
Marignolle Relais and Charme
A hotel room with a bed, a bedside table, a heater, a mirror, and a bathroom with a sink.

6. Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1,798 reviews)
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
United States
Debra
The price is P3,274
P4,099 total
includes taxes & fees
Nov 22 - Nov 23
Hu Firenze Camping In Town
A two-story house with a patio area, potted plants, and outdoor furniture.

7. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is P9,214
P10,420 total
includes taxes & fees
Nov 7 - Nov 8
La Locanda di Pietracupa
A stone building with a wooden door, a grill outside, and a stone wall.

8. Teranga in Chianti - Parking & Garden 3 BR

Teranga in Chianti - Parking & Garden 3 BR
Tavarnelle Val di Pesa
The price is P6,205
P24,892 total
includes taxes & fees
Nov 6 - Nov 7
Teranga in Chianti - Parking & Garden 3 BR
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

9. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is P17,227
P19,234 total
includes taxes & fees
Nov 13 - Nov 14
Terre di Baccio
A room with a dining table, a vase of flowers, a lamp, and a view of a historic building through a window.

10. Mamo Florence - Le Farine Della Signoria Apartments

Mamo Florence - Le Farine Della Signoria Apartments
Historic Centre of Florence
8.8 out of 10, Excellent, (11 reviews)
"Great host, amazing location!"
United States
raxshaaz
The price is P4,257
P10,160 total
includes taxes & fees
Nov 17 - Nov 18
Mamo Florence - Le Farine Della Signoria Apartments
A courtyard with stone steps leading to a covered patio area, featuring a stone fountain, outdoor seating, and a tiled roof.

11. Il Frantoio delle Grazie

Il Frantoio delle Grazie
Florence
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful place, picturesque country setting. Next time we stay here we will consider renting a car. The walk to the bus or train is only about a mile and it wasn’t too hot out. The kids really enjoyed the pool."
United States
Emily
The price is P7,042
P14,063 total
includes taxes & fees
Nov 7 - Nov 8
Il Frantoio delle Grazie
A terrace with a table set for breakfast, a chair, and a large umbrella.

12. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (270 reviews)
"Great location with a beautiful view."
United States
Erin
The price is P7,190
P8,479 total
includes taxes & fees
Nov 29 - Nov 30
Villa La Stella - Casa per Ferie
An open wooden door leading to an outdoor patio with a table and chairs.

13. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is P5,433
P8,110 total
includes taxes & fees
Nov 8 - Nov 9
Palazzo al Torrione 2
A balcony with a glass table, white curtains, and a bottle of champagne.

14. Dimora Bandinelli Firenze

Dimora Bandinelli Firenze
Oltrarno
9.8 out of 10, Exceptional, (191 reviews)
"We had a wonderful experience with hotel owners. Great hospitality, beautiful room, perfect location. Breakfast included, good selection of breakfast options. Highly recommend this place if you’re visiting Florence"
United States
Marat
The price is P5,194
P6,567 total
includes taxes & fees
Nov 24 - Nov 25
Dimora Bandinelli Firenze
A modern bedroom with a wooden ceiling, a bed with a white headboard, a beige sofa, and a glass-enclosed shower area with marble walls.

15. Residenza La Musa Amarcord

Residenza La Musa Amarcord
Historic Centre of Florence
10.0 out of 10, Exceptional, (181 reviews)
"The staff was super friendly and helped us with recommendations, acquiring a taxi, and booking dinner reservations! The room was very clean and had lovely Firenze charm. Definitely would stay again."
United States
Lauren
The price is P7,126
P8,692 total
includes taxes & fees
Nov 26 - Nov 27
Residenza La Musa Amarcord
A rooftop pool with a clear view of historic buildings and mountains in the background.

16. Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (151 reviews)
"Great property!"
United States
Jahzier
The price is P10,993
P12,946 total
includes taxes & fees
Nov 8 - Nov 9
Teatro Luxury Apartments Firenze - Starhotels Collezione
An open balcony with a table and chairs, a view of a tiled roof, and a door leading to the interior.

17. Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio
Historic Centre of Florence
9.0 out of 10, Wonderful, (281 reviews)
"Great location"
United States
Hatem
The price is P4,476
P5,777 total
includes taxes & fees
Dec 1 - Dec 2
Bob W Florence Ponte Vecchio
A balcony with wicker furniture, overlooking a historic square with a prominent tower and a clock.

18. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.6 out of 10, Exceptional, (891 reviews)
"The people were all extremely nice and helpful, location was amazing, exactly what we were after having never been to Florence !!"
United States
David
The price is P6,976
P8,527 total
includes taxes & fees
Nov 17 - Nov 18
Relais Piazza Signoria
An indoor swimming pool with clear water, a tiled floor, and a few lounge chairs along the side.

19. Forte16 View & Spa

Forte16 View & Spa
Santissima Annunziata
9.6 out of 10, Exceptional, (1,040 reviews)
"Great front desk Great perfect location Great room Great spa Great ammenties Awesome views Perfect for long stays."
United States
JENNIFER
The price is P6,576
P8,088 total
includes taxes & fees
Dec 1 - Dec 2
Forte16 View & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Calzaiolo Hotel Reviews

Bernini Palace

Bernini Palace

10/10 Excellent
"When we arrived it was evening the the Hotel Bernini Palace was twinkling! Such a beautiful lobby. Such a warm welcome by the staff. After a long journey we relaxed into their care and hospitality and our accommodations. Breakfast and the beautiful historical breakfast room was a treat. Service just perfect. Don't miss having a wonderful meal in the restaurant one evening. Delicious!"
donna 2-night trip
Posted less than an hour ago
Bernini Palace

Find out more about Calzaiolo

Search for holiday rentals in Calzaiolo on Expedia! You can easily find your home rentals, villas, holiday apartments in Calzaiolo using one of the methods below:

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Look no further and take a look at our great range of rental properties in Calzaiolo!

Frequently asked questions

Can I find vacation rentals in Calzaiolo?

Yes, there are vacation rentals close to popular attractions in Calzaiolo, or you can select a more remote option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Calzaiolo?

Villa La Stella - Casa per Ferie: This vacation home rental outside of Calzaiolo is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

What’s there to see and do in Calzaiolo?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Boboli Gardens. Other popular places to visit in the area include Piazza di Santa Maria Novella and Piazza del Duomo.

What’s a vacation rental in Calzaiolo like?

A vacation rental is a private property where you can stay for short or long periods in Calzaiolo. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a small group gathering.